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Just a quick tip - make sure you're tracking ALL your expenses related to your 1099 work! That can make a much bigger difference than investment losses. I do similar contract work and track things like: - Home office space - Internet/phone used for work - Computer equipment & software - Professional subscriptions - Mileage for any work travel - Professional development/training These deductions directly reduce your 1099 income before taxes are calculated, so they lower both income tax AND self-employment tax, which is huge!
What's the best app to track all this stuff? I've been trying to save receipts but it's getting messy.
I've had good luck with QuickBooks Self-Employed. It links to your bank account/credit cards and lets you swipe expenses as business or personal. It also has mileage tracking that runs in the background on your phone. There are cheaper options like Stride that are pretty good too. The key is finding something you'll actually use consistently. Even a simple spreadsheet works if you're diligent about updating it. The most important thing is keeping good records in case of an audit, so make sure whatever system you use allows you to store receipt images.
Great thread with lots of helpful advice! I'm also doing 1099 work for the first time this year and had similar questions about capital losses. One thing I want to add - if you're selling stocks at a loss specifically for tax purposes, be careful about the wash sale rule. If you buy back the same stock (or substantially identical securities) within 30 days before or after the sale, the IRS won't allow you to claim the loss for tax purposes. Also, since you mentioned you haven't been withholding taxes from your 1099 income, you might want to consider adjusting your W-2 withholding to cover some of the additional tax burden. You can submit a new W-4 to your employer to have extra taxes withheld from your regular paycheck. This can be easier than making quarterly estimated payments and helps ensure you're covered for the safe harbor rules others mentioned. The business expense tracking advice here is spot on too - those deductions can really add up and reduce both your income tax and self-employment tax burden!
Random question - has anyone used the new safe harbor for small rental activities? I think if your adjusted basis in the property is under a certain amount, you can potentially avoid some of the passive activity loss limitations. Worth looking into maybe?
I believe you're thinking of the small taxpayer safe harbor under the repair regulations (Revenue Procedure 2019-43), which allows certain taxpayers to deduct rather than capitalize expenses up to the lesser of $10,000 or 2% of the unadjusted basis of the building. This doesn't bypass passive activity loss rules though - just affects what can be immediately expensed vs depreciated.
One thing that might help clarify your situation - since you mentioned this is through an LLC partnership, make sure you understand your ownership percentage and how that affects the losses flowing through to you personally. If you're not a 100% owner, your K-1 will only show your proportionate share of the $38,000 in renovation expenses. Also, keep detailed records of any time you spend managing this rental property (even during renovation phase) - hours spent coordinating contractors, researching materials, visiting the property, etc. This documentation becomes crucial if you want to qualify for the active participation exception or potentially the real estate professional status in future years. The fact that you haven't had tenants yet doesn't disqualify you from the rental activity treatment, but it does mean you'll want to be extra careful about demonstrating that this is indeed intended as a rental business and not just a personal investment that might be reclassified by the IRS.
This is really helpful advice about documentation! I'm new to rental property investing and hadn't thought about tracking my time during the renovation phase. Since I've been doing most of the contractor coordination myself and spending weekends at the property overseeing work, I probably have way more hours than I realized. Should I be retroactively documenting the time I spent in 2024, or is it too late for that? And when you mention the risk of IRS reclassification - what would they potentially reclassify it as if not a rental activity? I definitely bought this property with the intention to rent it out, I just wanted to get it in good condition first.
Has anybody else tried using business expenses they don't have receipts for? I'm in a similar situation (got about $32k on 1099-NEC) and used some of my apartment for work, plus my personal laptop, but don't have specific receipts for those. FreeTaxUSA let me enter them, but now I'm nervous.
You don't actually need receipts for everything, but you should have some documentation. For the home office, measure the space and calculate the percentage of your home it represents. Keep those measurements. For the laptop, if you already owned it, estimate a fair market value when you started using it for business and the percentage of business use. Write this info down and keep it with your tax records. The IRS understands not everything has a receipt, especially things you already owned before starting the business. Just be reasonable with your claims.
The $4.5k-$5k tax bill is definitely normal for your situation! As others mentioned, self-employment tax is the big killer - you're paying both sides of Social Security and Medicare taxes (about 15.3%) plus regular income tax. A few things that might help going forward: 1. **Track everything better this year** - get a separate business checking account and run all business expenses through it. Makes record-keeping so much easier. 2. **Home office deduction** - if you use part of your living space exclusively for work, you can deduct that percentage of rent/utilities. Even a corner of your bedroom counts if it's your dedicated workspace. 3. **Equipment depreciation** - that laptop, desk, chair, etc. can be depreciated over several years rather than deducted all at once, which might spread out the benefit. 4. **Mileage** - track any driving for work (client meetings, picking up supplies, etc.) at 65.5 cents per mile for 2023. The phone at 50% business use sounds totally reasonable. I'd also look into whether any of your college courses relate to your work - sometimes continuing education can be deductible. Don't stress too much about this year's bill - it's a harsh welcome to self-employment taxes, but now you know what to expect and can plan accordingly!
Just a warning - don't skip reporting this! I didn't report $230 of excess scholarship income a few years ago because my tax software didn't prompt me to, and I got a letter from the IRS about 8 months later asking for additional tax payment plus a small penalty. Schools report the scholarship amounts to the IRS on form 1098-T, so they can match that against your return.
I had this exact same issue last year! The key is that most tax software doesn't automatically flag excess scholarships as taxable income, even though it should. What worked for me was manually entering it in the "Other Income" section. In most tax programs, look for something like "Other Income" or "Additional Income" - it's usually in the main income section but might be buried under "Less Common Income" or similar. Enter the $156 with a description like "Excess Scholarship" or just "SCH" and it should flow to Schedule 1, Line 8. The important thing is that this excess amount is definitely taxable income that needs to be reported. The IRS gets a copy of your 1098-T from your school, so they'll expect to see that excess amount somewhere on your return if it exists. Don't risk having to deal with correspondence from the IRS later - it's much easier to just add it now!
This is really helpful advice! I'm dealing with a similar situation where I have about $200 in excess scholarship that my tax software completely ignored. I've been going in circles trying to figure out where to enter it. Quick question - when you say "Other Income" section, is this typically found under the main income interview or is it usually buried somewhere else? I'm using FreeTaxUSA and I feel like I've clicked through every menu but might have missed it. Also, did you have any issues with the IRS accepting your return when you manually added the scholarship income this way?
Adriana Cohn
Has anyone figured out how to efficiently import historical data from UltraTax to CCH Axcess? We've got about 200 business clients and manually reentering prior year data seems incredibly inefficient.
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Jace Caspullo
ā¢Your firm's IT department or CCH implementation team should be handling this! There's a data conversion utility specifically for TR to CCH migrations. It won't be perfect (plan for about 80-85% accuracy), but it's way better than manual entry. Push back on management if they're expecting you to do this manually.
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Adriana Cohn
ā¢Thanks for the heads up! I just spoke with our IT department and apparently they are planning to use the conversion utility, but hadn't communicated that to our team yet. They're going to run a test batch next week. Much relieved I won't have to do all this manually. Appreciate the advice to push back - I was just accepting it as part of the merger pain.
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Amara Nwosu
Going through a similar transition myself right now! One thing that really helped me was creating a comparison spreadsheet mapping the key functions between UltraTax and CCH Axcess. For multi-state returns, I found that CCH's state selection interface is actually more streamlined once you get used to it - instead of having separate screens for each state like in UltraTax, everything flows through the main return with state-specific worksheets. A couple of practical tips: First, spend time in the CCH Axcess demo environment before working on live client files. Second, for Caseware integration, make sure you understand how the trial balance imports work - it's quite different from the Thomson Reuters flow. The working papers sync much better once you get the mapping right. Also, don't hesitate to use CCH's screen sharing support sessions. They're more helpful than the generic training modules for learning the nuances of complex returns. Good luck with the transition!
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Louisa Ramirez
ā¢That's really helpful advice about the demo environment! I hadn't thought about practicing there first before touching actual client files. Quick question - when you mention the trial balance import mapping being different, are you referring to the chart of accounts structure or something else? We have some clients with pretty customized GL accounts and I'm worried about how those will translate over from our current Thomson Reuters setup.
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